Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 62, Pages 16645-16651Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201803669
Keywords
alkynylation; amines; calcium carbide; copper; ketones
Categories
Funding
- Agency for Innovation by Science and Technology (IWT-Flanders)
- University of Antwerp (BOF)
- Hercules Foundation
Ask authors/readers for more resources
Calcium carbide was used in a Cu-I-catalysed three-component coupling with omega-chlorinated ketones and primary amines to generate terminal 2-alkynyl-N-heterocycles. The formation of an imine and the subsequent intramolecular substitution results in an active electrophilic iminium species, which can be alkynylated by in situ formed copper acetylide. A number of aliphatic primary (functionalised) amines and aliphatic or aromatic alkynes together with different alkyl- or aryl-substituted gamma- or delta-chloroketones could be used. Simple acid-base workup instead of column chromatography can be applied to obtain the resulting 2-alkynylpyrrolidines and 2-alkynylpiperidines.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available